[go: up one dir, main page]

WO2011093829A1 - Compositions effervescentes comprenant du cefixime et de l'acide clavulanique comme principes actifs - Google Patents

Compositions effervescentes comprenant du cefixime et de l'acide clavulanique comme principes actifs Download PDF

Info

Publication number
WO2011093829A1
WO2011093829A1 PCT/TR2011/000033 TR2011000033W WO2011093829A1 WO 2011093829 A1 WO2011093829 A1 WO 2011093829A1 TR 2011000033 W TR2011000033 W TR 2011000033W WO 2011093829 A1 WO2011093829 A1 WO 2011093829A1
Authority
WO
WIPO (PCT)
Prior art keywords
cefixime
pharmaceutical formulation
effervescent
formulation according
clavulanic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/TR2011/000033
Other languages
English (en)
Inventor
Mahmut Bilgic
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO2011093829A1 publication Critical patent/WO2011093829A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
    • A61K9/0007—Effervescent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients

Definitions

  • Present invention relates to effervescent formulations comprising cefixime and clavulanic acid and/or pharmaceutically acceptable salts, hydrates, enantiomers, racemates, organic salts, inorganic salts, esters, polymorphs, crystal forms and amorphous forms and/or combinations thereof suitable for oral use in treatment of infectious diseases caused by resistant bacteria
  • Antibiotics are one of the most frequently used medications used in medical practice and they form an important part of drug expenses. However in the last years the problem of resistant bacteria has become threatening. Due to use of high doses of antibiotics, the resistance problem has arisen and this became a problem for the civilization.
  • beta lactam antibiotics are combined with beta lactamase inhibitors to prevent enzymatic cleavage.
  • penicillin compositions comprising; beta lactamase inhibitors such as sulbactam, tazobactam, clavulanic acid and penicillin derivatives such as ampicillin, amoxycillin, ticarcillin, piperacillin are prepared to incorporate bacteria producing beta lactamase within their activity domain.
  • beta lactamase inhibitors such as sulbactam, tazobactam, clavulanic acid
  • penicillin derivatives such as ampicillin, amoxycillin, ticarcillin, piperacillin
  • WO97/09042 describes tablet formulations comprising amoxycillin and clavulanic acid in an amount in the ratio of 12:1 to 20: 1 preferably in the ratio of 14: 1.
  • Penicillin allergy is very common and 3-10 people out of 100 people are allergic to penicillin. Although this sensitivity to penicillin is mostly displayed with very mild reactions, death rate due to penicillin allergy is relatively high.
  • medications comprising combinations of beta-lactam and beta-lactamase are in capsule, tablet or suspension forms. When orally applied dosage forms are taken into consideration it is seen that bioavailability of the solution forms are higher than the other forms.
  • Cefixime shown with Formula (I) is a third generation cephalosporin antibiotic which is disclosed for the first time in the European patent numbered EP0030630 (Bl) and is indicated for use in treatment of infections caused by gram positive and gram negative bacteria.
  • medications comprising cefixime as the active agent are found in forms of suspensions and tablets.
  • Bioavailability of cefixime tablets are in the range of 40-50%.
  • Suspension forms provide 25-50% more bioavailability compared to the bioavailability of the tablet forms.
  • cefixime suspensions present in the state of the art are in the form of powder that is to be constituted with water prior to use.
  • the powder, once constituted, is unstable therefore is has to be consumed in 14 days.
  • cefixime is soluble in some of the organic solvents, it is very poorly soluble in water therefore solution forms of this compound were not developed.
  • Clavulanic acid is a beta- lactamase inhibitor shown with Formula (II):
  • Clavulanic acid and its derivatives are known as beta lactamase inhibitors that inhibit the activity of beta lactamase enzymes that is produced by the bacteria (e.g. GB 1508977).
  • Effervescent granule or tablet formulations prepared according to present invention comprising cefixime and clavulanic acid, have surprisingly formed a clear solution in water.
  • Said solution is prepared by constitution with water right before oral use, this way possibility of degradation is kept at a minimum level. Likewise, since these formulations are prepared right before use they do not require addition of anti-microbial agent, and this makes them safe to use for pediatric and non-pediatric patients.
  • cefixime and clavulanic acid have neutral taste, therefore formulations of the present invention can be sweetened upon request and this way solutions having pleasant taste can be obtained.
  • clavulanic acid used in the present invention relates to clavulanic acid and/or its pharmaceutically acceptable salts, hydrates, enantiomers, racemates, organic salts, inorganic salts, esters, polymorphs, crystal forms and amorphous forms and/or combinations thereof.
  • cefixime used in the present invention relates to cefixime and/or its pharmaceutically acceptable salts, hydrates, enantiomers, racemates, organic salts, inorganic salts, esters, polymorphs, crystal forms and amorphous forms and/or combinations thereof.
  • Clavulanic acid used in the formulation according to present invention is in the form of an alkali metal salt, preferably in the form of potassium clavulanate.
  • First aspect of the invention is related to a pharmaceutical formulation comprising therapeutically effective amount of cefixime and clavulanic acid.
  • Said invention is related to effervescent formulations that can easily form clear solutions in water in order to eliminate the technical disadvantages, such as low solubility and stability, arising from cefixime and clavulanic acid.
  • Formulations can be produced in the form of water dispersible effervescent granules and effervescent tablets.
  • Effervescent forms are more advantageous compared to the conventional forms due to the fact that they disperse more rapidly. Effervescent forms disperse rapidly and they simultaneously release the active agents into the aqueous medium.
  • the time interval between addition of the formulation into water or dispersion of the formulation and intake of the formulation is relatively short. The fact that the formulations are consumed in a short time prevents degradation of the active agents with water and also makes these formulations suitable for pediatric use since addition of antimicrobial agents is no longer necessary.
  • An aspect of the invention is to prepare effervescent tablet or granule that can be applied orally in the form of aqueous dispersion or solution.
  • Formulation disperse in aqueous medium in a rapid way and it can be applied orally or with a spoon or dropper if need be. Formulations of this sort are more advantageous due to the fact that they provide different using methods for old patients, children and babies.
  • Effervescent formulations according to present invention comprise effective amounts of cefixime, effective amounts of clavulanic acid, effervescent couple and at least one other pharmaceutically acceptable excipient.
  • Effervescent formulation comprises a mixture which upon getting in touch with water gives off carbon dioxide.
  • Effervescent compositions of this sort usually comprise an alkali or alkali earth metal carbonate or hydrogen carbonate, especially sodium hydrogen carbonate and an acid or acidic salt which upon contact with water gives off carbon dioxide.
  • Acid can be a pharmaceutically acceptable anhydrous organic or inorganic acid, preferably citric acid, monosodium citrate, tartaric acid, fumaric acid, malic acid, their salts or preferably a mixture thereof.
  • Alkali component that can be used in the present invention can be selected from but not limited with sodium, carbonates and bicarbonates of potassium and calcium and/or sodium glycine carbonate or a mixture thereof.
  • compositions according to present invention may comprise pharmaceutically acceptable excipients selected from a group comprising disintegrants, viscosity increasing agents, fillers, drying agents, lubricants, diluents, binders, glidants, anti-foaming agents, wetting agents, effervescent mixtures, sweeteners and flavoring agents.
  • Disintegrants used in the present invention provides easy and fast dispersion of the dosage form in the water.
  • Disintegrant can be selected from but not limited with polymers having high dispersion capacity such as cross linked hydroxypropyl cellulose, polyvinylpyrrolidone, high molecular weight polymers, microcrystalline cellulose, sodium starch glycolate, povidone, products known with trademarks Crospovidone®, Polyplasdone®.
  • polymers having high dispersion capacity such as cross linked hydroxypropyl cellulose, polyvinylpyrrolidone, high molecular weight polymers, microcrystalline cellulose, sodium starch glycolate, povidone, products known with trademarks Crospovidone®, Polyplasdone®.
  • Binders can be selected from, but not limited with, a group comprising potato, wheat or corn starch, microcrystalline cellulose for example products known with the trademarks Avicel®, Filtrak®, Heweten® or Pharmacel® hydroxypropyl cellulose, hydroxyethyl cellulose, hydroxypropylmethyl cellulose Type 2910 USP, hypromellose and polyvmylpyrolidone.for example Povidone® K30 (BASF).
  • Clavulanic acid and its derivatives are very sensitive to humidity.
  • potassium clavulanate can be used with a humidity absorbing agent, wherein ratio of potassium clavulanate to humidity absorbing agent is preferably in the ratio of 1 : 1.
  • Humidity absorbing agent has a large surface area and small pore volume, this way it would preserve its activity even under highly humid conditions and this provides improved flow properties to the compound.
  • colloidal silica such as colloidal silica anhydrous for example Aerosil®, magnesium trisilicate, powdered cellulose, Cabosil®, magnesium oxide, calcium silicate, Syloid®, starch, talk.
  • preferably Syloid® is used.
  • potassium clavulanate is preferably used with syloid in an amount in the ratio of 1 : 1.
  • magnesium stearate As lubricant one or more of magnesium stearate, aluminium stearate, calcium stearate, PEG 4000 - 8000 and/or talc can be used.
  • Sweetening agent can be selected from but not limited with a group comprising sodium chloride, aspartam, dextrose, fructose, sucralose, sodium cyclamate, mannitol, maltose, saccharide and/or pharmaceutically acceptable salts thereof.
  • Flavoring agents used in the present invention can be selected from a group comprising banana flavor, strawberry flavor, lemon flavor, orange flavor, peach flavor, vanilla flavor or similar natural fruits or might have the flavor of a natural herb.
  • Formulations according to present invention comprise;
  • effervescent couple preferably sodium hydrogen carbonate - citric acid; as sweetener preferably aspartam; as binder preferably PEG 6000 and at least one other pharmaceutically acceptable excipient is used.
  • Tablets, granules and/or powders according to invention may comprise cefixime and potassium clavunate in amounts up to maximum allowed daily dose in the unit dosage forms.
  • approximately 50 to 1000 mg of cefixime and approximately 20 to 300 mg of potassium clavulanate can be used.
  • Formulations according to present invention may preferably comprise 100 mg cefixime and 62.5 mg potassium clavulanate; 200 mg cefixime and 125 mg potassium clavulanate; 400 mg cefixime and 125 mg potassium clavulanate.
  • ratio of cefixime and potassium clavulanate is in the range of 1:0.01 to 1:10 by weight.
  • other amounts of these active agents in other ratios can be used as well.
  • potassium clavulanate is the most stable form of clavulanic acid, it is unstable against humidity. For this reason, formulations comprising clavulanic acid derivatives such as potassium clavulanate should be prepared under dry conditions, preferably at 0.5% relative humidity or at least at temperature of 60 °C. If applicable the components of the formulation may be dried beforehand.
  • Effervescent tablet formulations according to present invention may be shaped according to conventional tablet compression techniques.
  • Shape of the effervescent tablet may be one of the conventional shapes such as round, spherical, block or rectangular.
  • Formulations of the present invention can be used for the manufacture of a medicament for use in treatment of infections that are resistant to antibiotics.
  • Said infectious diseases are; upper respiratory tract infections (acute otitis media, acute sinusitis, acute streptococci tonsilo pharangitis), urinary tract infections, commonly acquired pneumonia and skin and soft tissue infections.
  • compositions of the present invention can be prepared by techniques known in the art; such as wet granulation or dry granulation. In addtion to the method which comprises dry or wet granulation of both of the active agents; the method given below which comprises wet granulation of only one of the active agents can be used. Said method comprises the steps of; a) Preparation of effervescent cefixime granulate by blending an effective amount of cefixime, effervescent couple and other pharmaceutically acceptable excipients, wet granulation of the mixture by the appropriate granulation solution and drying of the said granules at 60°C until humidity ratio is 0.5% and sieving said granules
  • the entire mixture can be separated in the form of two granulates.
  • the first granulate may comprise effective amount of cefixime, effervescent couple and at least one other pharmaceutically acceptable excipient and the second granulate may comprise clavulanic acid:syloid mixture.
  • these two granulates can be combined and mixed and may be optionally compressed in the form of tablets or filled into the sachets.
  • Granulates may comprise other pharmaceutically acceptable excipients.
  • the granulate comprising cefixime; effervescent couple, disintegrant, sweetener and effective amount of cefixime is mixed and is granulated with sufficient amount of deionized water.
  • the obtained granules are dried at 60°C to have humidity of 0.5% and sieved.
  • Effective amount of potassium clavulanate:syloid (1:1), lubricant and at least one other pharmaceutically acceptable excipients is added to the cefixime granulate and mixed, this way the final mixture is prepared.
  • the mixture is compressed in the form of tablets or filled into sachets.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des compositions effervescentes comprenant du cefixime et de l'acide clavulanique et/ou leurs sels, hydrates, énantiomères, racémates, sels organiques, sels inorganiques, esters, formes polymorphes, formes cristallines et formes amorphes pharmaceutiquement acceptables et/ou des combinaisons de ceux-ci, convenant à l'administration par voie orale dans le traitement de maladies infectieuses provoquées par des bactéries résistantes. En outre, comme ces principes actifs sont administrés aux patients extemporanément juste après leur dispersion dans l'eau, ils ont une durée de conservation plus longue que les suspensions et une biodisponibilité plus élevée. L'utilisation de compositions effervescentes est bien plus aisée, en particulier pour les patients gériatriques et pédiatriques qui ont des difficultés à avaler les gélules et les comprimés.
PCT/TR2011/000033 2010-01-29 2011-01-28 Compositions effervescentes comprenant du cefixime et de l'acide clavulanique comme principes actifs Ceased WO2011093829A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TR2010/00687A TR201000687A1 (tr) 2010-01-29 2010-01-29 Aktif madde olarak sefiksim ve klavulanik asit içeren efervesan formülasyonlar
TR2010/00687 2010-01-29

Publications (1)

Publication Number Publication Date
WO2011093829A1 true WO2011093829A1 (fr) 2011-08-04

Family

ID=43853203

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/TR2011/000026 Ceased WO2011093822A1 (fr) 2010-01-29 2011-01-28 Formulations effervescentes comprenant de la céfixime et de l'acide clavulanique comme agents actifs
PCT/TR2011/000033 Ceased WO2011093829A1 (fr) 2010-01-29 2011-01-28 Compositions effervescentes comprenant du cefixime et de l'acide clavulanique comme principes actifs

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/TR2011/000026 Ceased WO2011093822A1 (fr) 2010-01-29 2011-01-28 Formulations effervescentes comprenant de la céfixime et de l'acide clavulanique comme agents actifs

Country Status (3)

Country Link
EP (1) EP2528586A1 (fr)
TR (1) TR201000687A1 (fr)
WO (2) WO2011093822A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2568957A1 (fr) * 2010-05-14 2013-03-20 Mahmut Bilgic Composition pharmaceutique comprenant la céfixime et un composé dérivé de l'acide clavulanique
EP2575782A2 (fr) * 2010-06-03 2013-04-10 Mahmut Bilgic Formulations effervescentes comprenant de la céphalosporine et de l'acide clavulcanique
WO2013109229A1 (fr) * 2012-01-18 2013-07-25 Mahmut Bilgic Formulations en comprimés comprenant du céfixime utilisé comme agent actif
WO2014126541A1 (fr) * 2013-02-14 2014-08-21 Bilgiç Mahmut Compositions pharmaceutiques utilisées pour traiter des infections bactériennes

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1508977A (en) 1974-04-20 1978-04-26 Beecham Group Ltd Beta-lactam antibiotic from streptomyces clavuligerus
EP0030630B1 (fr) 1979-11-19 1987-04-01 Fujisawa Pharmaceutical Co., Ltd. Dérivés de l'acide 7-acylamino-3-vinyl céphalosporanique, procédé pour leur préparation, compositions pharmaceutiques les contenant; leurs produits de départ et leur préparation
WO1995028927A1 (fr) 1994-04-23 1995-11-02 Smithkline Beecham Corporation Comprime enrobe d'un polymere, comprenant de l'amoxycilline et du clavulanate
WO1997009042A1 (fr) 1995-09-07 1997-03-13 Smithkline Beecham Corporation Preparation pharmaceutique
WO2000003695A1 (fr) * 1998-07-17 2000-01-27 Lek Pharmaceutical & Chemical Co. Dd Preparation pharmaceutique a base de suspension comprenant amoxicilline, acide clavulanique et cellulose
WO2000050036A1 (fr) * 1999-02-26 2000-08-31 Biovail International Ltd. Composition sous forme de suspension a stockage stable a base d'amoxycilline et de clavulanate
EP1269996A1 (fr) 1999-04-13 2003-01-02 Beecham Pharmaceuticals (Pte) Limited Dose unitaire comprenant de l'amoxycilline et du clavulanate
CN1850087A (zh) * 2006-03-07 2006-10-25 中国药科大学 一种含有头孢克肟的泡腾片及制法
US20070134325A1 (en) * 1996-02-29 2007-06-14 Astellas Pharma Inc. Beta-lactam antibiotic-containing tablet and production thereof
WO2007129176A2 (fr) * 2006-04-28 2007-11-15 Wockhardt Ltd Traitement amélioré pour traiter des infections bactériennes résistantes

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5863894A (en) 1993-01-22 1994-08-15 Smithkline Beecham Plc Pharmaceutical formulations comprising clavulanic acid alone or in combination with other beta-lactam antibiotics
EP2568957A1 (fr) * 2010-05-14 2013-03-20 Mahmut Bilgic Composition pharmaceutique comprenant la céfixime et un composé dérivé de l'acide clavulanique

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1508977A (en) 1974-04-20 1978-04-26 Beecham Group Ltd Beta-lactam antibiotic from streptomyces clavuligerus
EP0030630B1 (fr) 1979-11-19 1987-04-01 Fujisawa Pharmaceutical Co., Ltd. Dérivés de l'acide 7-acylamino-3-vinyl céphalosporanique, procédé pour leur préparation, compositions pharmaceutiques les contenant; leurs produits de départ et leur préparation
WO1995028927A1 (fr) 1994-04-23 1995-11-02 Smithkline Beecham Corporation Comprime enrobe d'un polymere, comprenant de l'amoxycilline et du clavulanate
WO1997009042A1 (fr) 1995-09-07 1997-03-13 Smithkline Beecham Corporation Preparation pharmaceutique
US20070134325A1 (en) * 1996-02-29 2007-06-14 Astellas Pharma Inc. Beta-lactam antibiotic-containing tablet and production thereof
WO2000003695A1 (fr) * 1998-07-17 2000-01-27 Lek Pharmaceutical & Chemical Co. Dd Preparation pharmaceutique a base de suspension comprenant amoxicilline, acide clavulanique et cellulose
WO2000050036A1 (fr) * 1999-02-26 2000-08-31 Biovail International Ltd. Composition sous forme de suspension a stockage stable a base d'amoxycilline et de clavulanate
EP1269996A1 (fr) 1999-04-13 2003-01-02 Beecham Pharmaceuticals (Pte) Limited Dose unitaire comprenant de l'amoxycilline et du clavulanate
CN1850087A (zh) * 2006-03-07 2006-10-25 中国药科大学 一种含有头孢克肟的泡腾片及制法
WO2007129176A2 (fr) * 2006-04-28 2007-11-15 Wockhardt Ltd Traitement amélioré pour traiter des infections bactériennes résistantes

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
GAO Y ET AL: "Effervescent tablet containing cefixime and its preparing method", WPI / THOMSON,, vol. 2007, no. 29, 25 October 2006 (2006-10-25), XP002621234 *
MARTIN M A ET AL: "INCREASE IN THE ACTIVITY OF THIRD-GENERATION CEPHALOSPORINS IN COMBINATION WITH CLAVULANIC ACID AND SULBACTAM AGAINST BACTEROIDES-FRAGILIS", MEDICAL LABORATORY SCIENCES, ACADEMIC PRESS, LONDON, GB, vol. 47, no. 3, 1 January 1990 (1990-01-01), pages 163 - 167, XP008133356, ISSN: 0308-3616 *
RAWAT DEEPTI ET AL: "IN VITRO EVALUATION OF A NEW CEFIXIME-CLAVULANIC ACID COMBINATION FOR GRAM-NEGATIVE BACTERIA", SOUTHEAST ASIAN JOURNAL OF TROPICAL MEDICINE AND PUBLIC HEALTH, vol. 40, no. 1, January 2009 (2009-01-01), pages 131 - 139, XP002633201, ISSN: 0125-1562 *
SAUDAGAR P S ET AL: "Clavulanic acid: A review", BIOTECHNOLOGY ADVANCES, ELSEVIER PUBLISHING, BARKING, GB, vol. 26, no. 4, 1 July 2008 (2008-07-01), pages 335 - 351, XP027185702, ISSN: 0734-9750, [retrieved on 20080326] *

Also Published As

Publication number Publication date
WO2011093822A1 (fr) 2011-08-04
TR201000687A1 (tr) 2011-08-22
EP2528586A1 (fr) 2012-12-05

Similar Documents

Publication Publication Date Title
WO2011093826A2 (fr) Formulations effervescentes comprenant du céfaclor et de l'acide clavulanique comme principes actifs
US20060110445A1 (en) Dispersible tablet for oral administration
EP2568959A2 (fr) Formulations comprenant une céphalosporine et un acide clavulanique de troisième génération
WO2012060788A1 (fr) Formulations de céphalosporines avec teneur en humidité contrôlée
WO2011093829A1 (fr) Compositions effervescentes comprenant du cefixime et de l'acide clavulanique comme principes actifs
EP2566449B1 (fr) Compositions pharmaceutiques comprenant du ceftibutène
US20070014850A1 (en) Process for the preparation of dispersible tablets of cephalexin
WO2011139249A2 (fr) Composition pharmaceutique renfermant du cefdinir
EP2515860B1 (fr) Compositions pharmaceutiques améliorées comprenant cefdinir
US20130129791A1 (en) Preparations of effervescent formulations comprising second and third generation cephalosporin and uses thereof
WO2011093827A1 (fr) Formulations de cefdinir et d'acide clavulanique hydrodispersables destinées au traitement d'infections bactériennes
EP2528593A2 (fr) Formulations effervescentes contenant du cefprosil comme principe actif
WO2012060786A2 (fr) Formulations de proxétil cefpodoxime comprenant un agent de viscosité
EP2515858A1 (fr) Composition pharmaceutique très pure
EP2515905A1 (fr) Formulations pharmaceutiques comprenant une céphalosporine de troisième génération et de l'acide clavulanique
WO2011139251A1 (fr) Compositions pharmaceutiques comprenant du cefditorène pivoxil
EP2515859A1 (fr) Formulation effervescente à dispersion rapide
WO2012060791A2 (fr) Procédé de production de compositions pharmaceutiques comprenant du cefdinir
WO2012060787A1 (fr) Comprimés contenant du cefdinir
WO2012060792A1 (fr) Compositions pharmaceutiques comprenant au minimum 6% en poids de délitants
WO2012060793A2 (fr) Procédé de préparation de formulations de cefdinir
KR20040043589A (ko) 서방성 세파클러 제제 및 그 제조방법
WO2013151517A1 (fr) Formulations en comprimés comprenant du cefpodoxime proxétil et de l'acide clavulanique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11706047

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11706047

Country of ref document: EP

Kind code of ref document: A1